Anthracene dye and process of making same.



l discovered body (as described in the specification of Let- UNITED STATES PA'rnnT. OFFICE.

oscAR BALLY AND MAX HENRY ISLER, OFMANNHEIM,

GERMANY,

ASSIGNQRS-TO BADISCHE ANILIN & SODA FABRIK, OF LUDWIGS- HAFEN-ON-THE-RHINE, GERMANY, iA CORPORATION.

ANTHFlACENE DYE :AND PROCESS OF MAKING SAME.

Specifi'caticmof Letters Patent.

Patented May 8, 1906.

- Original application filed January 31,1905, Serial No. 243,671. Divided and this application filed October 11,1905- Sefial .To on whom if; may concern Be it known that we, OSCAR BALLY, doctor of philosophy and chemist, and MAX HENRY IsLER, chemist, 01 Republic, residing at Mannheim, in the Grand Duchy of Baden, German Empire, have invented certain new and useful Improvements in Anthracene Dyes and Processes of Making the Same, (which. invention is divided, pursuant to the requirement of the Patent Office, out of United States Letters Patent dated January 9, 1906, No. 809,892,) of which the following is a specification.

New compounds of the anthracene series containing a benz'anthrone group can beobtained by condensing certain anthracenecompounds with glycerin. (See Letters Patent Nos. 786,085,787,859, and798,104.) Wehave that these new henganthron'es upon being treated with caustic alkali yield valuable coloring-matters possessing dyeing properties similar to those of indanthrene, and We have described this invention in United States Letters Patent dated January 9, 1906, No. 809,892, which contains eneric claims for coloring-matters which can eproduced by treating a benzanthrone with caustic alkali and also for the process for producing the same.

n the present application we make no generic claim for the production of colorin matters from benzanthrones and for the -51- oring-matters themselves, but We wish to claim specifically the coloring-matters obtainable by treating with caustic alkali abenzanthrone which can be obtained by condensing with glycerin a naphthanthraquinone Patent No. 798,104) and the process for producing these coloring-matters, which are soluble in concentrated sulfuric acid, givin'- oliveeen solutions. They also dissolve in a kaline hydrosulfite, yielding reddish g broWn vats with a strong fluorescence, which dye vegeta; ble fiber substantively giving red-blue to green-blue shades. In particular, the coloring-matter obtainable from naphthanthra quinone yields a fuchsin-red vat with alkaline hydrosulfite. g

The following examples Will serve to furher illustrate the nature of our invention,

tizens of the Swiss I onehundred It dissolves Which, however, is not confined to these examples. The parts are by weight:

Example 1': Mix together ten (1.0) parts of the portion soluble in acetone otthe condensation product from naphthai'ithraquinone and glycerin and thirty (30) parts of solid caustic potash dissolved in thirty '(30) parts of absolute alcohol and heat the mixture for half an hour (thirty minutes) at a temperature of one hundred andfifty (150) degrees centigrade and then for another half-hour (thirty minutes) at a temperature of from and sixty-five (165) to one hundred and seventy (170) degrees centigrade. Boil the melt withwater and filter. The residue can be used directly as a paste for dyeing. in concentrated sulfuric acid, yielding an olive-green solution. With alkaline hydrosulfite it yields a reddish brown vat with a strong fluorescence, whichdyes vegetable fiber substantively giving reddish-blue shades which are extremely fast against the action of chlorin. I Example 2: Introduce five (5) parts of the condensation product from naphthanthrauinone and glycerin into. a mixture of ten parts of potassium parts of anhydrous sodium acetate, while maintaining the temperature at about two hundred (200) degrees centigrade, and continue heating at this temperature for from fifteen to thirty minutes. Work up the melt in the manner given in Example 1. The colorin -matter obtained dyes cotton more greenishshades Example 1.

Now what we claim is'- I a 1. The process for the production of anthracene coloring-matters by treating with caustic alkali a hereinbefore-defined'benzanthrone compound obtainable by condensing together a naphthanthraquinone body and glycerin.

, The process for the production of anthracene coloring-matters by treating with caustic alkali a hereinbeiore-defined benzanthrone compound obtainable by condensing together naphthanthraquinone and glycerin.

3. As new articles of manufacture, the anthracene coloring-matters which can be obhydrate and two (2) of blue than does the coloring-matter prepared as described in tained by treating with caustic alkali a benconcentrated sulfuric acid yielding an olivezanthrone obtainable from a naphthanthragreen solution, and which dissolves :in alkar5 quinone body, which coloringematters disline hydrosulfite, yielding a reddish-brown solve in concentrated sulfuric acid yielding vat which dyesvegetable fiber substantively i 5 olive-g1 een solutions, and which dissolve in yielding blue to green-blue shades.

10111113106116 coloring-matter which can be ob alkaline hydrosulfite yielding reddish-brown In testimony whereof we have hereunto set vats which dye vegetable fiber substantively our hands in the presence of two subscribing 29 giving red-blue to green-blue shades. Witnesses.

' OSCAR BALLY.

a new article of manufacture the any MAX HENRY ISLER. tained ytreating with caustic alkali the ben- Witnesses: zanthroneobtainable from naphthanthra- ERNEST F. EHRHARDT, ,quinone, which coloring-matter dissolves in J. Auto. LLoYD. 

